Trityl losartan

The title compound (systematic name: {2-butyl-4-chloro-1-[2'-(2-trityl-2H-tetrazol-5-yl)­bi­phenyl-4-yl­methyl]-1H-imidazol-5-yl}­methanol), C₄₁H₃₇ClN₆O, crystallizes in the centrosymmetric space group P with two independent mol­ecules in the asymmetric unit. These mol­ecules differ significantly only in the relative orientations of the rings in the bi­phenylyl­tetrazole moieties. One of the mol­ecules shows disorder for three C atoms in the n-butyl group. Hydro­gen bonds link the mol­ecules in an infinite chain along the a axis.

S1. Comment

Imidazole is a protonated five-membered ring, which promotes chemical reactions depending on the specific physical conditions at enzyme catalytic sites. Various imidazole derivatives are found to possess biological activity and are used in pharmaceuticals, agrochemicals, dyestuffs and high-temperature polymer products (Rasmussen, 1999).

The title compound, (I), trityl losartan, C₄₁H₃₇ClN₆O, is used as a key intermediate in the synthesis of losartan potassium, which is a very useful antihypertensive drug in the treatment of hypertension by inhibiting angiotensin II (Campbell et al., 1995). With a view to understanding the conformation of the imidazole moiety, the influence of the substituents at different positions of this five-membered ring and the effect of the trityl group on the losartan molecule as a whole, the crystal structure determination of (I) was carried out and the results are presented here. \sch

The asymmetric unit of (I) contains two crystallographically independent molecules (Figs. 1 and 2); they are distinguished by primes on the labels for the second molecule. The corresponding bond lengths and angles of both molecules agree with each other, but the orientation of the phenyl rings of the biphenyl moieties, and of the phenyl rings C41—C46 and C41'-C46', with respect to the tetrazole moieties is different in the unprimed molecule from that in the primed one. This can be seen from the C31—C32—C41—C42 and N1—C8—C31—C32 torsion angles of −52.0 (3) [−128.7 (2)° in the primed molecule] and −61.4 (3)° [50.5 (3)° in the primed molecul], respectively. Part of the n-butyl side chain of the unprimed molecule (atoms C57, C58 and C59) is disordered, with equal site-occupancy factors.

The crystal structure of (I) is stabilized by two intermolecular O—H···N hydrogen bonds linking different molecules alternately along the a axis, to form an infinite chain (Fig. 3). The same hydrogen-bond interaction was reported previously in the structure of losartan potassium (Fernández et al., 2002). Intramolecular C—H···N, C—H···O and C—H···π hydrogen bonds are observed and these have an influence on the conformation of the molecules and the crystal packing. The C14—H14···Cg(x + 1,y,z) (Cg denotes the centroid of the C1—C6 ring) interaction involves two phenyl rings of the trityl groups to form an infinite chain along the a direction. Details of the hydrogen-bonding geometry are given in Table 2.

S2. Experimental

The title compound was synthesized by condensing an equimolar mixture of 2-butyl-5-chloro-3H-imidazole-4-yl-methanol and 5-(4'-bromomethyl-biphenyl-2-yl)-1-trityl-1H-tetrazole with potassium carbonate in dimethylformamide with stirring at room temperature for 10 h, to give the title compound (80% yield). The compound was recrystallized from acetonitrile.

S3. Refinement

A free refinement of the occupancy factors for the disordered n-propyl group (atoms C57, C58 and C59) of the unprimed molecule gave values very close to 1/2, and these values were constrained. Atom C57B was refined isotropically because of unsatisfactory anisotropic behaviour. Most of the H atoms were located in difference Fourier syntheses and all were included at geometrically idealized positions and refined as riding, with C—H = 0.93, 0.96 and 0.97 Å, and O—H = 0.82 Å. The U_iso(H) values were set at 1.2 (1.5 for hydroxy groups) times U_eq of the atoms to which they were bonded.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1990); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and Mercury (Version 1.2.1; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2004).

Figures

	Fig. 1. A view of the unprimed molecule of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. A view of the primed molecule of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 3. The packing of the molecules of (I) in the unit cell, showing the intermolecular hydrogen bonds (dashed lines) along the a axis. H atoms have been omitted for clarity.

2-butyl-4-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]- 1H-imidazol-5-ylmethanol

Crystal data

C41H37ClN6O	Z = 4
Mr = 665.22	F(000) = 1400
Triclinic, P1	Dx = 1.238 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6962 (3) Å	Cell parameters from 13199 reflections
b = 20.5493 (6) Å	θ = 2.9–30.0°
c = 21.7392 (5) Å	µ = 0.15 mm^−1
α = 69.597 (2)°	T = 293 K
β = 88.587 (2)°	Prism, colourless
γ = 78.962 (3)°	0.55 × 0.23 × 0.16 mm
V = 3570.0 (2) Å^3

Data collection

Kuma KM4 CCD area-detector diffractometer	9584 reflections with I > 2σ(I)
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 2.9°
Detector resolution: 8.2356 pixels mm^-1	h = −10→10
ω scans	k = −24→24
48342 measured reflections	l = −25→25
12560 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0744P)^2 + 0.3025P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
12560 reflections	Δρmax = 0.42 e Å^−3
909 parameters	Δρmin = −0.43 e Å^−3
6 restraints	Extinction correction: SHELXTL/PC (Sheldrick, 1990), FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl	0.83482 (10)	0.35159 (5)	0.56482 (4)	0.1071 (3)
N1	0.58748 (17)	0.30731 (7)	0.16329 (7)	0.0443 (4)
N2	0.55668 (15)	0.24949 (7)	0.20996 (7)	0.0410 (3)
N3	0.42286 (18)	0.26129 (8)	0.23759 (9)	0.0609 (5)
N4	0.36372 (18)	0.32950 (8)	0.20973 (10)	0.0635 (5)
N5	1.0015 (2)	0.32769 (10)	0.40728 (8)	0.0633 (5)
N6	0.9039 (2)	0.26347 (11)	0.49829 (9)	0.0710 (5)
O	1.1474 (2)	0.45038 (10)	0.41466 (10)	0.1022 (6)
H1	1.1983	0.4278	0.4493	0.153*
C1	0.58671 (19)	0.12512 (9)	0.28228 (9)	0.0416 (4)
C2	0.5749 (2)	0.13589 (10)	0.34216 (10)	0.0521 (5)
H2	0.6069	0.1749	0.3463	0.062*
C3	0.5162 (3)	0.08936 (12)	0.39543 (11)	0.0657 (6)
H3	0.5065	0.0978	0.4348	0.079*
C4	0.4720 (3)	0.03054 (12)	0.39047 (12)	0.0698 (6)
H4	0.4313	−0.0006	0.4262	0.084*
C5	0.4883 (3)	0.01808 (11)	0.33271 (12)	0.0652 (6)
H5	0.4608	−0.0223	0.3297	0.078*
C6	0.5452 (2)	0.06483 (9)	0.27855 (10)	0.0503 (5)
H6	0.5555	0.0557	0.2395	0.060*
C7	0.65751 (19)	0.17661 (8)	0.22454 (9)	0.0399 (4)
C8	0.4667 (2)	0.35671 (9)	0.16553 (9)	0.0438 (4)
C11	0.82693 (19)	0.17551 (9)	0.24559 (8)	0.0395 (4)
C12	0.9162 (2)	0.10973 (10)	0.28243 (10)	0.0541 (5)
H12	0.8699	0.0701	0.2958	0.065*
C13	1.0724 (2)	0.10252 (11)	0.29937 (11)	0.0563 (5)
H13	1.1303	0.0582	0.3239	0.068*
C14	1.1423 (2)	0.16064 (11)	0.28010 (9)	0.0507 (5)
H14	1.2477	0.1559	0.2909	0.061*
C15	1.0548 (2)	0.22569 (10)	0.24470 (9)	0.0488 (5)
H15	1.1014	0.2653	0.2321	0.059*
C16	0.8980 (2)	0.23352 (10)	0.22732 (9)	0.0446 (4)
H16	0.8406	0.2781	0.2033	0.054*
C21	0.6519 (2)	0.15993 (9)	0.16105 (9)	0.0443 (4)
C22	0.5073 (3)	0.16896 (11)	0.12991 (10)	0.0599 (5)
H22	0.4161	0.1871	0.1466	0.072*
C23	0.4975 (3)	0.15128 (12)	0.07447 (12)	0.0781 (7)
H23	0.4003	0.1575	0.0541	0.094*
C24	0.6326 (4)	0.12439 (13)	0.04936 (12)	0.0851 (8)
H24	0.6264	0.1126	0.0120	0.102*
C25	0.7756 (3)	0.11514 (13)	0.07965 (12)	0.0778 (7)
H25	0.8664	0.0969	0.0629	0.093*
C26	0.7855 (3)	0.13291 (11)	0.13510 (10)	0.0584 (5)
H26	0.8831	0.1266	0.1552	0.070*
C31	0.4502 (2)	0.43271 (9)	0.12589 (9)	0.0447 (4)
C32	0.5616 (2)	0.47079 (9)	0.13347 (9)	0.0453 (4)
C33	0.5463 (3)	0.54073 (10)	0.09164 (10)	0.0604 (5)
H33	0.6208	0.5665	0.0949	0.073*
C34	0.4243 (3)	0.57292 (11)	0.04549 (11)	0.0689 (6)
H34	0.4174	0.6197	0.0180	0.083*
C35	0.3128 (3)	0.53603 (11)	0.03993 (11)	0.0660 (6)
H35	0.2293	0.5579	0.0092	0.079*
C36	0.3252 (2)	0.46632 (10)	0.08015 (10)	0.0577 (5)
H36	0.2490	0.4415	0.0767	0.069*
C41	0.6879 (2)	0.43964 (9)	0.18652 (9)	0.0451 (4)
C42	0.6521 (2)	0.40884 (11)	0.25165 (9)	0.0538 (5)
H42	0.5481	0.4072	0.2619	0.065*
C43	0.7673 (2)	0.38066 (12)	0.30141 (10)	0.0592 (5)
H43	0.7399	0.3602	0.3445	0.071*
C44	0.9238 (2)	0.38241 (11)	0.28789 (9)	0.0535 (5)
C45	0.9599 (2)	0.41389 (11)	0.22323 (10)	0.0561 (5)
H45	1.0637	0.4162	0.2131	0.067*
C46	0.8448 (2)	0.44181 (11)	0.17356 (10)	0.0546 (5)
H46	0.8724	0.4625	0.1305	0.066*
C51	1.0557 (3)	0.35046 (14)	0.34005 (10)	0.0724 (6)
H51	1.1202	0.3100	0.3327	0.087*
H52	1.1209	0.3851	0.3355	0.087*
C52	0.9633 (2)	0.37120 (13)	0.44384 (11)	0.0640 (6)
C53	0.9905 (3)	0.44488 (13)	0.42344 (14)	0.0838 (7)
H53	0.9309	0.4730	0.3826	0.101*
H54	0.9509	0.4648	0.4565	0.101*
C54	0.9045 (3)	0.32957 (14)	0.49874 (11)	0.0677 (6)
C55	0.9643 (3)	0.26388 (13)	0.44147 (11)	0.0684 (6)
C56	0.9925 (3)	0.20274 (15)	0.41877 (15)	0.1025 (9)
H56A	0.9920	0.2201	0.3712	0.123*	0.50
H56B	0.9072	0.1772	0.4319	0.123*	0.50
H56C	0.9113	0.2121	0.3853	0.123*	0.50
H56D	1.0910	0.2035	0.3968	0.123*	0.50
C57A	1.1446 (4)	0.1526 (2)	0.4454 (2)	0.0731 (13)	0.50
H57A	1.1469	0.1131	0.4306	0.088*	0.50
H57B	1.2268	0.1767	0.4232	0.088*	0.50
C58A	1.1939 (11)	0.1213 (5)	0.5168 (2)	0.094 (3)	0.50
H58A	1.1745	0.1594	0.5343	0.113*	0.50
H58B	1.3065	0.1042	0.5200	0.113*	0.50
C59A	1.1194 (14)	0.0611 (6)	0.5621 (6)	0.115 (3)	0.50
H59A	1.0093	0.0782	0.5642	0.138*	0.50
H59B	1.1684	0.0442	0.6053	0.138*	0.50
H59C	1.1337	0.0231	0.5451	0.138*	0.50
C57B	0.9956 (7)	0.1293 (2)	0.4632 (3)	0.1029 (18)*	0.50
H57C	1.0091	0.0979	0.4382	0.123*	0.50
H57D	0.8971	0.1263	0.4850	0.123*	0.50
C58B	1.1280 (11)	0.1073 (7)	0.5133 (5)	0.124 (4)	0.50
H58C	1.1197	0.1381	0.5389	0.149*	0.50
H58D	1.2294	0.1045	0.4938	0.149*	0.50
C59B	1.096 (3)	0.0350 (7)	0.5534 (10)	0.223 (11)	0.50
H59D	1.1307	0.0028	0.5305	0.268*	0.50
H59E	0.9856	0.0382	0.5597	0.268*	0.50
H59F	1.1517	0.0180	0.5953	0.268*	0.50
Cl'	0.46271 (8)	0.28975 (4)	0.41202 (3)	0.0861 (2)
N1'	0.01949 (17)	0.18282 (7)	0.85749 (7)	0.0432 (3)
N2'	0.09379 (18)	0.20010 (7)	0.90044 (7)	0.0447 (4)
N3'	0.1405 (2)	0.14615 (9)	0.95568 (8)	0.0702 (5)
N4'	0.0951 (2)	0.09108 (9)	0.94926 (8)	0.0682 (5)
N5'	0.4494 (2)	0.25262 (10)	0.59763 (8)	0.0612 (5)
N6'	0.3444 (2)	0.33792 (10)	0.50660 (9)	0.0669 (5)
O'	0.7616 (2)	0.15726 (10)	0.58754 (8)	0.0905 (5)
H1'	0.8048	0.1895	0.5656	0.136*
C1'	0.0183 (2)	0.32853 (9)	0.83479 (8)	0.0430 (4)
C2'	−0.0772 (2)	0.38426 (10)	0.84717 (10)	0.0541 (5)
H2'	−0.0793	0.3853	0.8896	0.065*
C3'	−0.1696 (3)	0.43836 (11)	0.79765 (11)	0.0647 (6)
H3'	−0.2339	0.4750	0.8073	0.078*
C4'	−0.1675 (3)	0.43872 (12)	0.73493 (11)	0.0686 (6)
H4'	−0.2292	0.4755	0.7017	0.082*
C5'	−0.0730 (3)	0.38388 (12)	0.72121 (10)	0.0649 (6)
H5'	−0.0709	0.3839	0.6784	0.078*
C6'	0.0192 (2)	0.32864 (11)	0.77055 (9)	0.0525 (5)
H6'	0.0816	0.2917	0.7608	0.063*
C7'	0.1343 (2)	0.27133 (9)	0.88747 (8)	0.0430 (4)
C8'	0.0218 (2)	0.11443 (9)	0.88948 (9)	0.0464 (4)
C11'	0.3018 (2)	0.27023 (10)	0.86234 (9)	0.0493 (5)
C12'	0.3468 (3)	0.33438 (13)	0.82886 (11)	0.0659 (6)
H12'	0.2735	0.3763	0.8199	0.079*
C13'	0.4979 (3)	0.33714 (18)	0.80862 (13)	0.0861 (8)
H13'	0.5261	0.3806	0.7871	0.103*
C14'	0.6059 (3)	0.2759 (2)	0.82026 (15)	0.0955 (9)
H14'	0.7078	0.2776	0.8068	0.115*
C15'	0.5634 (3)	0.21194 (19)	0.85195 (16)	0.0971 (9)
H15'	0.6363	0.1702	0.8590	0.117*
C16'	0.4117 (3)	0.20900 (13)	0.87373 (12)	0.0727 (6)
H16'	0.3848	0.1654	0.8961	0.087*
C21'	0.1218 (2)	0.28316 (9)	0.95391 (8)	0.0470 (4)
C22'	−0.0123 (3)	0.27418 (11)	0.98938 (10)	0.0625 (5)
H22'	−0.0917	0.2582	0.9743	0.075*
C23'	−0.0292 (3)	0.28884 (13)	1.04713 (11)	0.0759 (7)
H23'	−0.1198	0.2830	1.0704	0.091*
C24'	0.0883 (4)	0.31192 (13)	1.06979 (11)	0.0819 (8)
H24'	0.0766	0.3226	1.1081	0.098*
C25'	0.2224 (3)	0.31924 (12)	1.03619 (11)	0.0748 (7)
H25'	0.3027	0.3339	1.0522	0.090*
C26'	0.2394 (3)	0.30502 (10)	0.97839 (10)	0.0568 (5)
H26'	0.3311	0.3103	0.9558	0.068*
C31'	−0.0510 (2)	0.07011 (9)	0.86242 (9)	0.0480 (4)
C32'	−0.0196 (2)	0.06901 (9)	0.79914 (9)	0.0492 (4)
C33'	−0.1054 (3)	0.03251 (12)	0.77397 (12)	0.0653 (6)
H33'	−0.0911	0.0334	0.7312	0.078*
C34'	−0.2114 (3)	−0.00499 (12)	0.81152 (14)	0.0747 (7)
H34'	−0.2673	−0.0293	0.7940	0.090*
C35'	−0.2345 (3)	−0.00651 (12)	0.87450 (14)	0.0735 (7)
H35'	−0.3034	−0.0331	0.9001	0.088*
C36'	−0.1559 (2)	0.03129 (10)	0.89998 (11)	0.0607 (5)
H36'	−0.1733	0.0308	0.9425	0.073*
C41'	0.1078 (2)	0.10234 (10)	0.76160 (9)	0.0490 (5)
C42'	0.0833 (3)	0.14993 (12)	0.69830 (10)	0.0653 (6)
H42'	−0.0142	0.1599	0.6768	0.078*
C43'	0.2017 (3)	0.18328 (13)	0.66609 (10)	0.0701 (6)
H43'	0.1823	0.2154	0.6233	0.084*
C44'	0.3481 (2)	0.16954 (11)	0.69653 (9)	0.0554 (5)
C45'	0.3755 (2)	0.11860 (11)	0.75863 (10)	0.0553 (5)
H45'	0.4749	0.1065	0.7791	0.066*
C46'	0.2580 (2)	0.08550 (10)	0.79069 (10)	0.0535 (5)
H46'	0.2792	0.0514	0.8324	0.064*
C51'	0.4768 (3)	0.20955 (13)	0.66724 (10)	0.0723 (6)
H51'	0.4885	0.2401	0.6915	0.087*
H52'	0.5747	0.1758	0.6728	0.087*
C52'	0.5055 (2)	0.23051 (11)	0.54638 (10)	0.0557 (5)
C53'	0.6168 (3)	0.16307 (12)	0.55589 (13)	0.0787 (7)
H53'	0.5681	0.1241	0.5817	0.094*
H54'	0.6369	0.1586	0.5133	0.094*
C54'	0.4392 (2)	0.28437 (11)	0.49235 (10)	0.0582 (5)
C55'	0.3529 (3)	0.31707 (12)	0.57125 (12)	0.0666 (6)
C56'	0.2685 (4)	0.35805 (17)	0.61071 (15)	0.0957 (9)
H56'	0.1760	0.3891	0.5852	0.115*
H57'	0.2333	0.3251	0.6498	0.115*
C57'	0.3607 (4)	0.40139 (17)	0.63116 (16)	0.1120 (11)
H58'	0.2958	0.4237	0.6581	0.134*
H59'	0.4498	0.3698	0.6587	0.134*
C58'	0.4187 (4)	0.4562 (2)	0.57896 (19)	0.1171 (11)
H60'	0.3338	0.4828	0.5466	0.141*
H61'	0.5002	0.4339	0.5574	0.141*
C59'	0.4837 (5)	0.5069 (2)	0.6021 (2)	0.1554 (16)
H62'	0.4226	0.5151	0.6370	0.186*
H63'	0.4792	0.5508	0.5663	0.186*
H64'	0.5906	0.4870	0.6178	0.186*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1062 (5)	0.1461 (7)	0.0854 (5)	−0.0067 (5)	0.0150 (4)	−0.0711 (5)
N1	0.0435 (8)	0.0363 (8)	0.0516 (9)	−0.0061 (7)	0.0016 (7)	−0.0145 (7)
N2	0.0317 (7)	0.0368 (8)	0.0556 (9)	−0.0075 (6)	0.0014 (6)	−0.0170 (7)
N3	0.0383 (9)	0.0442 (9)	0.0943 (13)	−0.0086 (7)	0.0170 (9)	−0.0178 (9)
N4	0.0391 (9)	0.0445 (9)	0.0975 (14)	−0.0041 (7)	0.0150 (9)	−0.0162 (9)
N5	0.0591 (11)	0.0810 (13)	0.0504 (10)	−0.0074 (9)	−0.0069 (8)	−0.0265 (10)
N6	0.0712 (12)	0.0840 (14)	0.0555 (11)	−0.0081 (10)	−0.0057 (9)	−0.0246 (10)
O	0.0950 (14)	0.0911 (13)	0.0953 (14)	−0.0316 (11)	−0.0254 (11)	0.0075 (10)
C1	0.0322 (9)	0.0391 (9)	0.0518 (11)	−0.0063 (7)	−0.0007 (8)	−0.0139 (8)
C2	0.0465 (11)	0.0541 (11)	0.0576 (12)	−0.0117 (9)	0.0011 (9)	−0.0210 (9)
C3	0.0634 (13)	0.0757 (15)	0.0521 (12)	−0.0099 (12)	0.0059 (10)	−0.0173 (11)
C4	0.0678 (14)	0.0600 (14)	0.0656 (15)	−0.0155 (11)	0.0073 (11)	−0.0009 (11)
C5	0.0693 (14)	0.0437 (11)	0.0752 (15)	−0.0184 (10)	0.0042 (12)	−0.0080 (10)
C6	0.0504 (11)	0.0417 (10)	0.0585 (12)	−0.0112 (8)	0.0021 (9)	−0.0160 (9)
C7	0.0339 (9)	0.0350 (9)	0.0519 (10)	−0.0062 (7)	−0.0011 (8)	−0.0166 (8)
C8	0.0362 (9)	0.0413 (10)	0.0572 (11)	−0.0076 (8)	−0.0041 (8)	−0.0210 (8)
C11	0.0341 (9)	0.0409 (9)	0.0469 (10)	−0.0087 (7)	0.0037 (7)	−0.0190 (8)
C12	0.0399 (10)	0.0453 (11)	0.0761 (14)	−0.0106 (8)	−0.0017 (9)	−0.0186 (10)
C13	0.0405 (10)	0.0507 (11)	0.0738 (14)	−0.0016 (9)	−0.0063 (9)	−0.0201 (10)
C14	0.0324 (9)	0.0674 (13)	0.0580 (12)	−0.0105 (9)	0.0019 (8)	−0.0285 (10)
C15	0.0408 (10)	0.0585 (12)	0.0535 (11)	−0.0211 (9)	0.0059 (9)	−0.0220 (9)
C16	0.0395 (10)	0.0459 (10)	0.0488 (10)	−0.0105 (8)	0.0023 (8)	−0.0158 (8)
C21	0.0494 (11)	0.0350 (9)	0.0468 (10)	−0.0096 (8)	−0.0021 (8)	−0.0114 (8)
C22	0.0608 (13)	0.0562 (12)	0.0628 (13)	−0.0082 (10)	−0.0130 (10)	−0.0215 (10)
C23	0.0966 (19)	0.0645 (14)	0.0718 (16)	−0.0102 (13)	−0.0336 (14)	−0.0225 (12)
C24	0.125 (2)	0.0721 (16)	0.0594 (15)	−0.0047 (16)	−0.0121 (15)	−0.0319 (13)
C25	0.0935 (19)	0.0769 (16)	0.0656 (15)	−0.0052 (14)	0.0094 (14)	−0.0347 (13)
C26	0.0606 (13)	0.0570 (12)	0.0607 (13)	−0.0100 (10)	0.0053 (10)	−0.0255 (10)
C31	0.0453 (10)	0.0395 (9)	0.0499 (10)	−0.0019 (8)	−0.0011 (8)	−0.0196 (8)
C32	0.0509 (11)	0.0403 (10)	0.0466 (10)	−0.0085 (8)	0.0029 (8)	−0.0178 (8)
C33	0.0717 (14)	0.0438 (11)	0.0640 (13)	−0.0145 (10)	0.0011 (11)	−0.0148 (10)
C34	0.0882 (17)	0.0436 (11)	0.0620 (14)	−0.0017 (11)	−0.0040 (12)	−0.0080 (10)
C35	0.0738 (15)	0.0534 (13)	0.0617 (13)	0.0094 (11)	−0.0171 (11)	−0.0190 (10)
C36	0.0546 (12)	0.0518 (12)	0.0691 (13)	0.0026 (9)	−0.0134 (10)	−0.0297 (10)
C41	0.0490 (11)	0.0416 (10)	0.0495 (11)	−0.0133 (8)	0.0011 (8)	−0.0195 (8)
C42	0.0446 (11)	0.0709 (13)	0.0509 (11)	−0.0177 (10)	0.0044 (9)	−0.0244 (10)
C43	0.0555 (12)	0.0809 (15)	0.0432 (11)	−0.0189 (11)	0.0038 (9)	−0.0213 (10)
C44	0.0492 (11)	0.0647 (12)	0.0520 (12)	−0.0127 (9)	−0.0002 (9)	−0.0259 (10)
C45	0.0468 (11)	0.0691 (13)	0.0572 (12)	−0.0218 (10)	0.0052 (9)	−0.0227 (10)
C46	0.0560 (12)	0.0620 (12)	0.0486 (11)	−0.0225 (10)	0.0072 (9)	−0.0173 (9)
C51	0.0575 (13)	0.1066 (19)	0.0532 (13)	−0.0138 (13)	−0.0017 (10)	−0.0290 (13)
C52	0.0533 (12)	0.0788 (15)	0.0605 (13)	−0.0023 (11)	−0.0082 (10)	−0.0302 (12)
C53	0.0795 (18)	0.0752 (17)	0.0904 (19)	−0.0060 (14)	−0.0185 (14)	−0.0245 (14)
C54	0.0619 (14)	0.0829 (16)	0.0621 (14)	−0.0006 (12)	−0.0059 (11)	−0.0366 (13)
C55	0.0701 (14)	0.0815 (16)	0.0562 (13)	−0.0030 (12)	−0.0088 (11)	−0.0328 (12)
C56	0.106 (2)	0.114 (2)	0.105 (2)	−0.0031 (18)	−0.0147 (17)	−0.0683 (19)
C57A	0.068 (3)	0.079 (3)	0.074 (3)	0.004 (2)	−0.005 (2)	−0.037 (3)
C58A	0.091 (7)	0.101 (6)	0.085 (5)	0.016 (5)	−0.004 (4)	−0.041 (4)
C59A	0.091 (6)	0.120 (8)	0.103 (6)	0.020 (5)	0.013 (4)	−0.022 (6)
C58B	0.094 (8)	0.124 (8)	0.122 (8)	0.010 (6)	0.014 (5)	−0.021 (6)
C59B	0.209 (17)	0.139 (12)	0.26 (2)	0.004 (11)	0.005 (13)	−0.020 (12)
Cl'	0.0969 (5)	0.1075 (5)	0.0554 (3)	−0.0237 (4)	0.0122 (3)	−0.0290 (3)
N1'	0.0502 (9)	0.0416 (8)	0.0413 (8)	−0.0144 (7)	0.0033 (7)	−0.0160 (7)
N2'	0.0574 (9)	0.0423 (8)	0.0359 (8)	−0.0155 (7)	0.0008 (7)	−0.0123 (7)
N3'	0.1101 (15)	0.0519 (10)	0.0463 (10)	−0.0271 (10)	−0.0149 (10)	−0.0071 (8)
N4'	0.1054 (15)	0.0487 (10)	0.0482 (10)	−0.0269 (10)	−0.0080 (10)	−0.0070 (8)
N5'	0.0623 (11)	0.0694 (12)	0.0479 (10)	−0.0212 (9)	0.0135 (8)	−0.0120 (8)
N6'	0.0651 (11)	0.0665 (11)	0.0627 (12)	−0.0113 (9)	0.0114 (9)	−0.0162 (9)
O'	0.0778 (12)	0.0907 (12)	0.0743 (11)	0.0050 (9)	0.0039 (9)	−0.0047 (9)
C1'	0.0470 (10)	0.0455 (10)	0.0391 (9)	−0.0189 (8)	0.0059 (8)	−0.0130 (8)
C2'	0.0609 (12)	0.0533 (11)	0.0486 (11)	−0.0117 (10)	0.0057 (9)	−0.0184 (9)
C3'	0.0653 (14)	0.0543 (12)	0.0664 (14)	−0.0043 (10)	0.0019 (11)	−0.0147 (11)
C4'	0.0661 (14)	0.0665 (14)	0.0582 (14)	−0.0107 (11)	−0.0058 (11)	−0.0040 (11)
C5'	0.0730 (14)	0.0782 (15)	0.0398 (11)	−0.0218 (12)	−0.0008 (10)	−0.0124 (11)
C6'	0.0593 (12)	0.0584 (12)	0.0425 (10)	−0.0179 (10)	0.0053 (9)	−0.0181 (9)
C7'	0.0521 (11)	0.0426 (10)	0.0383 (9)	−0.0169 (8)	0.0041 (8)	−0.0155 (8)
C8'	0.0543 (11)	0.0425 (10)	0.0434 (10)	−0.0139 (8)	0.0109 (9)	−0.0145 (8)
C11'	0.0480 (11)	0.0611 (12)	0.0445 (10)	−0.0148 (9)	0.0005 (8)	−0.0233 (9)
C12'	0.0574 (13)	0.0757 (15)	0.0678 (14)	−0.0273 (11)	0.0094 (11)	−0.0220 (12)
C13'	0.0665 (16)	0.120 (2)	0.0791 (17)	−0.0481 (17)	0.0124 (13)	−0.0284 (16)
C14'	0.0538 (15)	0.146 (3)	0.095 (2)	−0.0302 (19)	0.0143 (14)	−0.048 (2)
C15'	0.0544 (15)	0.122 (3)	0.121 (2)	0.0035 (16)	0.0014 (15)	−0.060 (2)
C16'	0.0577 (14)	0.0771 (16)	0.0864 (17)	−0.0101 (12)	0.0030 (12)	−0.0339 (13)
C21'	0.0635 (12)	0.0432 (10)	0.0351 (9)	−0.0137 (9)	0.0010 (9)	−0.0130 (8)
C22'	0.0779 (15)	0.0685 (14)	0.0459 (11)	−0.0251 (11)	0.0116 (11)	−0.0210 (10)
C23'	0.1075 (19)	0.0721 (15)	0.0483 (12)	−0.0234 (14)	0.0249 (13)	−0.0198 (11)
C24'	0.143 (3)	0.0667 (15)	0.0427 (12)	−0.0248 (16)	0.0048 (15)	−0.0254 (11)
C25'	0.109 (2)	0.0681 (15)	0.0561 (13)	−0.0241 (14)	−0.0095 (14)	−0.0288 (11)
C26'	0.0758 (14)	0.0504 (11)	0.0501 (11)	−0.0177 (10)	−0.0044 (10)	−0.0214 (9)
C31'	0.0533 (11)	0.0378 (10)	0.0533 (11)	−0.0131 (8)	0.0055 (9)	−0.0145 (8)
C32'	0.0535 (11)	0.0419 (10)	0.0546 (11)	−0.0123 (9)	0.0028 (9)	−0.0185 (9)
C33'	0.0719 (14)	0.0647 (13)	0.0730 (14)	−0.0226 (11)	0.0044 (12)	−0.0364 (11)
C34'	0.0705 (15)	0.0674 (15)	0.102 (2)	−0.0295 (12)	0.0023 (14)	−0.0402 (14)
C35'	0.0703 (15)	0.0577 (13)	0.0966 (19)	−0.0319 (12)	0.0155 (13)	−0.0225 (13)
C36'	0.0659 (13)	0.0514 (12)	0.0654 (13)	−0.0232 (10)	0.0135 (11)	−0.0157 (10)
C41'	0.0589 (12)	0.0475 (11)	0.0470 (11)	−0.0148 (9)	0.0071 (9)	−0.0226 (9)
C42'	0.0643 (13)	0.0857 (16)	0.0477 (12)	−0.0261 (12)	−0.0026 (10)	−0.0192 (11)
C43'	0.0743 (15)	0.0883 (16)	0.0412 (11)	−0.0286 (13)	0.0011 (11)	−0.0079 (11)
C44'	0.0581 (12)	0.0648 (13)	0.0442 (11)	−0.0176 (10)	0.0099 (9)	−0.0177 (10)
C45'	0.0504 (11)	0.0601 (12)	0.0534 (12)	−0.0071 (10)	0.0045 (9)	−0.0195 (10)
C46'	0.0577 (12)	0.0492 (11)	0.0481 (11)	−0.0084 (9)	0.0070 (9)	−0.0115 (9)
C51'	0.0740 (15)	0.0875 (16)	0.0489 (12)	−0.0294 (13)	0.0078 (11)	−0.0092 (11)
C52'	0.0560 (12)	0.0580 (12)	0.0556 (12)	−0.0210 (10)	0.0127 (10)	−0.0182 (10)
C53'	0.0873 (18)	0.0603 (14)	0.0862 (17)	−0.0203 (13)	0.0192 (15)	−0.0207 (13)
C54'	0.0596 (12)	0.0640 (13)	0.0513 (12)	−0.0194 (11)	0.0131 (10)	−0.0175 (10)
C55'	0.0614 (13)	0.0706 (15)	0.0642 (14)	−0.0116 (12)	0.0162 (11)	−0.0207 (12)
C56'	0.097 (2)	0.103 (2)	0.0896 (19)	−0.0075 (17)	0.0259 (16)	−0.0445 (17)
C57'	0.146 (3)	0.099 (2)	0.086 (2)	−0.001 (2)	0.015 (2)	−0.0406 (18)
C58'	0.094 (2)	0.154 (3)	0.132 (3)	−0.044 (2)	0.034 (2)	−0.078 (3)
C59'	0.164 (4)	0.190 (4)	0.159 (4)	−0.074 (3)	0.011 (3)	−0.098 (3)

Geometric parameters (Å, º)

Cl—C54	1.715 (2)	C53—H53	0.97
O—C53	1.393 (3)	C53—H54	0.97
O—H1	0.82	C56—H56A	0.97
N1—C8	1.327 (2)	C56—H56C	0.97
N1—N2	1.335 (2)	C56—H56B	0.97
N2—N3	1.316 (2)	C56—H56D	0.97
N2—C7	1.514 (2)	C57A—H57A	0.97
N3—N4	1.320 (2)	C57A—H57B	0.97
N4—C8	1.346 (3)	C57B—H57C	0.97
N5—C51	1.467 (3)	C57B—H57D	0.97
N5—C52	1.382 (3)	C58A—H58A	0.97
N5—C55	1.359 (3)	C58A—H58B	0.97
N6—C54	1.363 (4)	C58B—H58C	0.97
N6—C55	1.328 (3)	C59A—H59A	0.96
Cl'—C54'	1.720 (2)	C59A—H59B	0.96
O'—C53'	1.415 (3)	C59A—H59C	0.96
O'—H1'	0.82	C59B—H59D	0.96
N1'—C8'	1.330 (2)	C59B—H59E	0.96
N1'—N2'	1.328 (2)	C59B—H59F	0.96
N2'—N3'	1.327 (2)	C1'—C2'	1.383 (3)
N2'—C7'	1.500 (2)	C1'—C6'	1.396 (3)
N3'—N4'	1.319 (2)	C1'—C7'	1.541 (2)
N4'—C8'	1.347 (2)	C2'—C3'	1.381 (3)
N5'—C51'	1.461 (3)	C3'—C4'	1.361 (3)
N5'—C52'	1.388 (3)	C4'—C5'	1.379 (4)
N5'—C55'	1.362 (3)	C5'—C6'	1.388 (3)
N6'—C54'	1.365 (3)	C7'—C11'	1.542 (3)
N6'—C55'	1.318 (3)	C7'—C21'	1.544 (2)
C1—C2	1.393 (3)	C8'—C31'	1.480 (3)
C1—C6	1.384 (3)	C11'—C12'	1.391 (3)
C1—C7	1.536 (3)	C11'—C16'	1.375 (3)
C2—C3	1.379 (3)	C12'—C13'	1.381 (4)
C3—C4	1.375 (4)	C13'—C14'	1.366 (5)
C4—C5	1.365 (3)	C14'—C15'	1.371 (5)
C5—C6	1.385 (3)	C15'—C16'	1.396 (4)
C7—C11	1.547 (2)	C21'—C22'	1.388 (3)
C7—C21	1.538 (3)	C21'—C26'	1.379 (3)
C8—C31	1.478 (3)	C22'—C23'	1.388 (3)
C11—C12	1.395 (3)	C23'—C24'	1.373 (4)
C12—C13	1.383 (3)	C24'—C25'	1.366 (4)
C13—C14	1.374 (3)	C25'—C26'	1.384 (3)
C14—C15	1.371 (3)	C31'—C32'	1.403 (3)
C11—C16	1.379 (3)	C31'—C36'	1.387 (3)
C15—C16	1.388 (3)	C32'—C41'	1.490 (3)
C21—C22	1.393 (3)	C32'—C33'	1.393 (3)
C21—C26	1.384 (3)	C33'—C34'	1.381 (4)
C22—C23	1.384 (3)	C34'—C35'	1.369 (4)
C23—C24	1.383 (4)	C35'—C36'	1.378 (3)
C24—C25	1.371 (4)	C41'—C42'	1.375 (3)
C25—C26	1.385 (3)	C41'—C46'	1.393 (3)
C31—C32	1.402 (3)	C42'—C43'	1.386 (4)
C31—C36	1.391 (3)	C43'—C44'	1.383 (3)
C32—C33	1.390 (3)	C44'—C45'	1.382 (3)
C32—C41	1.492 (3)	C44'—C51'	1.512 (3)
C33—C34	1.375 (3)	C45'—C46'	1.376 (3)
C34—C35	1.371 (4)	C52'—C53'	1.482 (3)
C35—C36	1.379 (3)	C52'—C54'	1.349 (3)
C41—C42	1.390 (3)	C55'—C56'	1.490 (4)
C41—C46	1.392 (3)	C56'—C57'	1.484 (5)
C42—C43	1.380 (3)	C57'—C58'	1.452 (5)
C43—C44	1.390 (3)	C58'—C59'	1.504 (6)
C44—C45	1.384 (3)	C2'—H2'	0.93
C44—C51	1.513 (3)	C3'—H3'	0.93
C45—C46	1.378 (3)	C4'—H4'	0.93
C52—C53	1.486 (4)	C5'—H5'	0.93
C52—C54	1.358 (3)	C6'—H6'	0.93
C55—C56	1.480 (4)	C12'—H12'	0.93
C56—C57A	1.499 (5)	C13'—H13'	0.93
C56—C57B	1.477 (6)	C14'—H14'	0.93
C57A—C58A	1.496 (6)	C15'—H15'	0.93
C57B—C58B	1.495 (12)	C16'—H16'	0.93
C58A—C59A	1.532 (15)	C22'—H22'	0.93
C58B—C59B	1.51 (2)	C23'—H23'	0.93
C2—H2	0.93	C24'—H24'	0.93
C3—H3	0.93	C25'—H25'	0.93
C4—H4	0.93	C26'—H26'	0.93
C5—H5	0.93	C33'—H33'	0.93
C6—H6	0.93	C34'—H34'	0.93
C12—H12	0.93	C35'—H35'	0.93
C13—H13	0.93	C36'—H36'	0.93
C14—H14	0.93	C42'—H42'	0.93
C15—H15	0.93	C43'—H43'	0.93
C16—H16	0.93	C45'—H45'	0.93
C22—H22	0.93	C46'—H46'	0.93
C23—H23	0.93	C51'—H51'	0.97
C24—H24	0.93	C51'—H52'	0.97
C25—H25	0.93	C53'—H53'	0.97
C26—H26	0.93	C53'—H54'	0.97
C33—H33	0.93	C56'—H56'	0.97
C34—H34	0.93	C56'—H57'	0.97
C35—H35	0.93	C57'—H58'	0.97
C36—H36	0.93	C57'—H59'	0.97
C42—H42	0.93	C58'—H60'	0.97
C43—H43	0.93	C58'—H61'	0.97
C45—H45	0.93	C59'—H62'	0.96
C46—H46	0.93	C59'—H63'	0.96
C51—H51	0.97	C59'—H64'	0.96
C51—H52	0.97
C53—O—H1	109	Cl—C54—C52	127.5 (2)
C53'—O'—H1'	109	N6—C54—C52	113.1 (2)
N1—N2—N3	113.10 (13)	Cl—C54—N6	119.48 (18)
N2—N1—C8	102.27 (14)	N5—C55—C56	124.0 (2)
N1—N2—C7	123.07 (14)	N6—C55—C56	125.0 (2)
N3—N2—C7	123.56 (13)	N5—C55—N6	110.9 (2)
N2—N3—N4	106.39 (14)	C55—C56—C57A	113.3 (3)
N3—N4—C8	106.39 (15)	C55—C56—C57B	123.0 (3)
C51—N5—C55	126.7 (2)	C56—C57A—C58A	123.9 (5)
C52—N5—C55	108.31 (18)	C56—C57A—C58B	109.8 (5)
C51—N5—C52	124.7 (2)	C56—C57B—C58B	109.4 (6)
C54—N6—C55	104.3 (2)	C57A—C58A—C59A	119.3 (8)
N1'—N2'—N3'	113.30 (15)	C57B—C58B—C59B	98.0 (12)
N2'—N1'—C8'	102.06 (14)	C2'—C1'—C6'	118.03 (17)
N1'—N2'—C7'	124.70 (14)	C6'—C1'—C7'	119.43 (17)
N3'—N2'—C7'	121.84 (15)	C2'—C1'—C7'	122.25 (16)
N2'—N3'—N4'	106.25 (15)	C1'—C2'—C3'	121.19 (19)
N3'—N4'—C8'	106.21 (16)	C2'—C3'—C4'	120.7 (2)
C51'—N5'—C55'	127.0 (2)	C3'—C4'—C5'	119.3 (2)
C52'—N5'—C55'	107.95 (18)	C4'—C5'—C6'	120.8 (2)
C51'—N5'—C52'	124.7 (2)	C1'—C6'—C5'	120.0 (2)
C54'—N6'—C55'	104.52 (19)	N2'—C7'—C11'	108.90 (15)
C2—C1—C7	119.44 (17)	N2'—C7'—C21'	105.59 (13)
C6—C1—C7	122.07 (17)	N2'—C7'—C1'	109.76 (14)
C2—C1—C6	118.30 (18)	C1'—C7'—C21'	111.40 (15)
C1—C2—C3	120.7 (2)	C11'—C7'—C21'	111.93 (14)
C2—C3—C4	120.2 (2)	C1'—C7'—C11'	109.18 (14)
C3—C4—C5	119.6 (2)	N1'—C8'—C31'	123.35 (16)
C4—C5—C6	120.8 (2)	N4'—C8'—C31'	124.46 (17)
C1—C6—C5	120.28 (19)	N1'—C8'—N4'	112.18 (17)
N2—C7—C1	107.30 (14)	C7'—C11'—C12'	118.61 (19)
C11—C7—C21	111.88 (14)	C12'—C11'—C16'	118.1 (2)
N2—C7—C21	106.01 (14)	C7'—C11'—C16'	123.29 (19)
C1—C7—C11	108.26 (14)	C11'—C12'—C13'	121.4 (3)
N2—C7—C11	110.61 (14)	C12'—C13'—C14'	119.9 (3)
C1—C7—C21	112.68 (15)	C13'—C14'—C15'	119.7 (3)
N4—C8—C31	124.20 (17)	C14'—C15'—C16'	120.5 (3)
N1—C8—N4	111.78 (17)	C11'—C16'—C15'	120.4 (3)
N1—C8—C31	123.99 (16)	C7'—C21'—C22'	120.07 (17)
C12—C11—C16	118.17 (16)	C22'—C21'—C26'	118.42 (18)
C7—C11—C12	116.77 (16)	C7'—C21'—C26'	121.47 (16)
C7—C11—C16	124.93 (16)	C21'—C22'—C23'	120.7 (2)
C11—C12—C13	121.06 (19)	C22'—C23'—C24'	119.8 (2)
C12—C13—C14	120.2 (2)	C23'—C24'—C25'	120.1 (2)
C13—C14—C15	119.18 (17)	C24'—C25'—C26'	120.3 (2)
C14—C15—C16	121.15 (19)	C21'—C26'—C25'	120.7 (2)
C11—C16—C15	120.27 (18)	C8'—C31'—C36'	118.67 (17)
C7—C21—C22	119.31 (17)	C32'—C31'—C36'	120.23 (18)
C7—C21—C26	122.29 (17)	C8'—C31'—C32'	121.06 (16)
C22—C21—C26	118.33 (19)	C31'—C32'—C41'	120.98 (17)
C21—C22—C23	120.8 (2)	C33'—C32'—C41'	120.99 (18)
C22—C23—C24	119.9 (2)	C31'—C32'—C33'	117.95 (18)
C23—C24—C25	119.9 (2)	C32'—C33'—C34'	121.1 (2)
C24—C25—C26	120.3 (2)	C33'—C34'—C35'	120.2 (2)
C21—C26—C25	120.8 (2)	C34'—C35'—C36'	120.2 (2)
C32—C31—C36	119.86 (18)	C31'—C36'—C35'	120.2 (2)
C8—C31—C36	119.92 (17)	C32'—C41'—C42'	122.35 (18)
C8—C31—C32	120.21 (16)	C32'—C41'—C46'	119.83 (17)
C31—C32—C33	117.66 (18)	C42'—C41'—C46'	117.82 (19)
C33—C32—C41	120.24 (18)	C41'—C42'—C43'	121.0 (2)
C31—C32—C41	122.02 (17)	C42'—C43'—C44'	121.0 (2)
C32—C33—C34	121.9 (2)	C43'—C44'—C45'	117.96 (18)
C33—C34—C35	120.1 (2)	C45'—C44'—C51'	118.20 (17)
C34—C35—C36	119.6 (2)	C43'—C44'—C51'	123.76 (19)
C31—C36—C35	120.83 (19)	C44'—C45'—C46'	120.98 (17)
C32—C41—C42	120.77 (16)	C41'—C46'—C45'	121.04 (19)
C32—C41—C46	121.96 (17)	N5'—C51'—C44'	114.29 (19)
C42—C41—C46	117.25 (17)	N5'—C52'—C54'	103.46 (19)
C41—C42—C43	121.49 (17)	C53'—C52'—C54'	132.9 (2)
C42—C43—C44	120.83 (18)	N5'—C52'—C53'	123.63 (19)
C45—C44—C51	118.83 (17)	O'—C53'—C52'	114.0 (2)
C43—C44—C51	123.23 (18)	Cl'—C54'—N6'	120.24 (16)
C43—C44—C45	117.94 (17)	Cl'—C54'—C52'	126.69 (18)
C44—C45—C46	121.17 (17)	N6'—C54'—C52'	113.07 (19)
C41—C46—C45	121.32 (18)	N5'—C55'—C56'	124.1 (2)
N5—C51—C44	113.6 (2)	N6'—C55'—C56'	124.9 (2)
N5—C52—C54	103.4 (2)	N5'—C55'—N6'	111.0 (2)
C53—C52—C54	132.3 (2)	C55'—C56'—C57'	115.5 (3)
N5—C52—C53	124.3 (2)	C56'—C57'—C58'	116.7 (3)
O—C53—C52	114.1 (2)	C57'—C58'—C59'	113.9 (3)
N1—C8—C31—C32	−61.4 (3)	N1'—C8'—C31'—C32'	50.5 (3)
C31—C32—C41—C42	−52.0 (3)	C31'—C32'—C41'—C42'	−128.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O—H1···N6′^i	0.82	2.04	2.775 (3)	149
O′—H1′···N6	0.82	2.02	2.832 (3)	170
C16—H16···N1	0.93	2.28	2.945 (2)	128
C16′—H16′···N3′	0.93	2.49	3.124 (3)	126
C51—H52···O	0.97	2.56	3.240 (3)	127
C51′—H52′···O′	0.97	2.52	3.218 (3)	129
C14—H14···Cg^i	0.93	2.67	3.518 (2)	152

Symmetry code: (i) x+1, y, z.